Bologna is a great call. Much underrated medieval city (feat. thousand year old university) and a glorious foodie heaven. Much-neglected ancient artworks just left to basically/criminally rot on outdoor walls. Oh, and for purposes of football tourism, a very decent Serie A team. Smashing place...
Tried Funchal in Madeira in September a few years back. Expected it to be fairly dull (somebody else booked it) but it was actually pretty decent. Banana plantations in the middle of town, a Ronaldo museum the size of an aircraft hangar, cable-cars, that thing where you slide down the streets in...